SRN1 and Stille Reactions: A New Synthetic Strategy

Eduardo F Corsico,Roberto A Rossi

doi:10.3390/50300431

Abstract

The photostimulated reaction of Me3Sn- ion with mono, di and trichloro arenes in liquid ammonia gave very good yields of stannanes by the SRN1 mechanism. These products reacted by a palladium-catalized cross coupling reaction with halobenzenes to give phenylated products also in very goods yields. Similar yields can be obtained in one-pot reactions.

Highlights

The radical nucleophilic substitution, or SRN1 reaction, is a process through which a nucleophilic substitution is obtained [1]
We thought that the photostimulated reaction of mono, diand trichloro- arenes with Me3Sn- ions in liquid ammonia to synthesize the trimethylarylstannanes followed by the Pd(0) cross coupling reaction with haloarenes (Stille Reaction) [2,3] would be an important approach for the synthesis of arylated or polyarylated compounds [4]
We undertook the study of the palladium catalyzed reaction of trimethylarylstannanes, synthesized by the SRN1 mechanism, with mono, di- and trichloro- arenes as a model reaction for this methodology

Summary

Introduction

The radical nucleophilic substitution, or SRN1 reaction, is a process through which a nucleophilic substitution is obtained [1]. The scope of the process has considerably increased and nowadays it is an important synthetic possibility to achieve substitution of different substrates. Several nucleophiles can be used, such as carbanions and anions from compounds bearing heteroatoms, which react to form new C-C or C-heteroatom bonds in good yields.

Results

Conclusion